In vitro antiparasitic activity of new thiosemicarbazones in strains of Trypanosoma cruzi

In this study thiosemicarbazones derivatives of 5-[(trifluoromethyl)phenylthio]-2-furaldehyde were synthesized and evaluated in terms of their efficiency in challenging the growth of epimastigote forms of Trypanosoma cruzi, the etiological agent of Chagas' disease. A number of compounds were sy...

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Bibliographic Details
Published in:European journal of medicinal chemistry 2014-11, Vol.87, p.23-29
Main Authors: Moreno-Rodríguez, Adriana, Salazar-Schettino, Paz María, Bautista, Juan Luis, Hernández-Luis, Francisco, Torrens, Hugo, Guevara-Gómez, Yolanda, Pina-Canseco, Socorro, Torres, Martha Bucio, Cabrera-Bravo, Margarita, Martinez, Cesar Mendoza, Pérez-Campos, Eduardo
Format: Article
Language:English
Subjects:
Apoptosis
Apoptosis - drug effects
Blood Platelets - drug effects
Blood Platelets - parasitology
Cells, Cultured
Chagas Disease - drug therapy
Flow Cytometry
Humans
In Vitro Techniques
Molecular Structure
Monocytes - drug effects
Monocytes - parasitology
Platelet activation
Platelet Activation - drug effects
Structure–activity relationship
Thiosemicarbazones
Thiosemicarbazones - chemistry
Trypanocidal activity
Trypanocidal Agents - chemistry
Trypanocidal Agents - pharmacology
Trypanosoma cruzi - drug effects
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Summary:In this study thiosemicarbazones derivatives of 5-[(trifluoromethyl)phenylthio]-2-furaldehyde were synthesized and evaluated in terms of their efficiency in challenging the growth of epimastigote forms of Trypanosoma cruzi, the etiological agent of Chagas' disease. A number of compounds were synthesized from 5-bromo-2-furfuraldehyde using nucleophilic aromatic substitution, with a series of trifluoromethyl thiolates, followed by condensation reactions with thiosemicarbazide. Their molecular structures were determined by 1H, 13C and 19F NMR, MS and IR spectroscopy. When tested with T. cruzi, they showed a stronger reaction, similar to nifurtimox and benznidazole, with the 5-[nitro-4-(trifluoromethyl)phenyltio]-2-furaldehyde thiosemicarbazone (compound 4) showing the highest antiparasitic activity. This improved activity may be explained due to the nitro group present in the molecule, which potentiates its activity. The thiosemicarbazone derivatives in this study showed no apoptosis in platelets or monocytes, nor did they induce platelet activation. The trypanocidal activity of these substances represents a good starting point for a medicinal chemistry program aimed at therapy for Chagas' disease. New thiosemicarbazone derivatives with trypanocidal activity were synthesized which may act as a potential agent in Chagas' disease. [Display omitted] •New thiosemicarbazones with trypanocidal activity were synthesized.•These produced no apoptosis in platelets or monocytes, nor in platelet activation.•Of the five thiosemicarbazones, only one has significant activity in Trypanosoma cruzi.
ISSN:0223-5234
1768-3254
DOI:10.1016/j.ejmech.2014.09.027